


How to Train Your Maid

by BrittanyChayanne



Category: How to Train Your Dragon (Movies)
Genre: Crossdressing, Forced Crossdressing, M/M, Maids, Tricked Into Slavery, also Dagur's last name is Caton because fuck it, shameless excuse to put Hiccup in a maid dress, this is really just a shounen maid kuro-kun au, yay for pointless porn aus
Language: English
Status: In-Progress
Published: 2015-03-08
Updated: 2015-03-08
Packaged: 2018-03-16 22:04:39
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 1,573
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3504392
Author URL: https://archiveofourown.org/users/BrittanyChayanne/pseuds/BrittanyChayanne
Summary: <blockquote class="userstuff">
              <p>Left with thousands of dollars of debt from his father's gambling habits, Hiccup agrees to serve as a maid to Dagur, a wealthy man who seems to have more than just cleaning on his mind...</p><p>ON HIATUS</p>
            </blockquote>





	1. Prologue

Hiccup growled in frustration as he stumbled again, tugging the short black skirt of his outfit further down. It didn't help at all, but it made him feel better. Why Dagur had decided that he should wear freaking _heels_ today, he didn't know, but he was sure he was going to break an ankle. He held on to the railing of the curved staircase tightly as he carefully went downstairs to the dining room. If there was one upside to these stupid shoes, they added enough to his height that he could reach the other side of the huge table without having to walk all the way around the ridiculous thing. Honestly, who needed a table _this_ big? No one was even visiting this idiot!

Leaning over, he grumbled under his breath as he scrubbed the wood until it shined. Hiccup nearly screamed when something suddenly pressed against his bottom. He straightened up sharply, his head slamming into something and sending his hairpiece falling over his eyes. Twisting around to see who had come up behind him, he gave an annoyed groan when he saw his boss.

“Dammit Dagur, I told you not to sneak up on me!” He snapped, pulling the lacy headband off his face and flattening his hair before putting it back where it belonged. “I'm busy Dagur.” He muttered, knowing the excuse wouldn't work.

“Is that any way to talk to me?” Dagur all but purred, his lips pressing to the soft skin just under Hiccup's ear. His hand rubbed over Hiccup's thigh, playing with the edge of his panties and making him quickly cover his mouth to muffle a small squeak.

“N-No.. Master. I'm sorry.” Hiccup said quietly. Dagur smirked as his hand moved from Hiccup's leg to his ass.

“Good boy.” He stepped away and dropped in to one of the chairs. Hiccup looked at him curiously. “Don't stop just for me.” Dagur said with a grin, waving his hand. Hiccup had to fight the urge to roll his eyes as he snatched the rag he'd dropped.

He could feel Dagur's eyes on him as he worked his way down the table, fighting the urge to hold his skirt down with one hand as he bent over to clean the opposite side. The lace and silk panties that brushed against his skin had him flushing.

This really was _not_ what he had been expecting when the man had offered to let him work off the debt he had ended up with. Housework, he could do. Cleaning around the huge ass house, helping with meals, that was easy. But Dagur failed to inform him that ‘maid’ was code for ‘personal fuck toy’.

It all had started about two months ago…


	2. Chapter 2

**Notes for the Chapter:**

> This story has a blog to go along with it! Come on over and ask something at howtotrainyourmaid.tumblr.com !

_“Name?” The voice crackled through the speaker at the gate. Hiccup jumped slightly._

_“Ah- H-Hiccup Haddock. Mister Caton is expecting me?”_

_There was a silence before a sound buzzed and the gate slid open. Hiccup hesitated for a moment before stepping through it, flinching slightly when it slammed shut behind him. He hiked his bag further up on his shoulder, his few meager possessions pressing against his back as he walked up the long drive way to the large house. When he reached the door, he lifted the huge knocker with both hands, dropping it with a_ thud _against the wood._

_There was silence for a moment before the door swung open and a large man appeared before him. He didn’t say a word, just grunted and turned. Hiccup frowned curiously, but assumed he was supposed to follow him. He was lead through a few twisting halls before the man opened a door. He was shoved through roughly, a slight sound of pain escaping as he stumbled into the room._

_It was a large - at least to him - sitting room, with several couches and seats scattered around a roaring fireplace. A man he recognized as Dagur Caton was sitting in one of the chairs, a tumblr of scotch in his hand. Hiccup hesitated just past the doorway, unsure of what to do. He cleared his throat nervously and the man looked up, grinning at him._

_“Ah, Hiccup. I’m glad to see you made it. Please, sit.” He waved to the chair across from him. Hiccup hesitated for a few more seconds, almost unwilling to sit on such a clean looking piece of furniture, but eventually the temptation was too great and he plopped down on the edge of the seat. “I hope your journey was safe.”_

_“Ah.. Mostly, I guess.” Hiccup shrugged. He had spent most of the trip on an uncomfortable bus, the only one he could afford after scraping together every penny he had been able to find._

_“I was sorry to hear about your father’s passing. He was a good man.”_

_Hiccup grimaced. His father was hardly a good man. “Of course. What with the drinking, the gambling addiction, the hundreds of thousands of dollars of debt..” He muttered._

_“Yes.. About that.”_

_“I’m sorry, Mister Caton, but I can’t pay you back. At- At least, not right now. My dad’s life insurance was barely enough to have him cremated.” Hiccup was ashamed of the tears that began to well in his eyes. His life had crashed around him when his father died, the bank foreclosing on his home when he couldn’t manage the steep payments on his meager barely-part-time job. He was ashamed to admit that he had been sleeping in an alley for the last two weeks, washing in a rec center before his job and going back to his street every night to huddle up under his only blanket._

_“I don’t want to wait to be repaid, Hiccup.” Hiccup’s eyes shot up and he trembled slightly. Was Dagur going to kill him? “No, I’m not going to kill you.” Dagur rolled his eyes. Shit, did Hiccup say that out loud? “I want to offer you a job, Hiccup.”_

Hiccup shuddered when Dagur’s hand brushed across his leg again, his nails scraping lightly on his skin. “D.. Dagur. I’m trying to clean.” He reprimanded. The man smirked and grabbed his hips suddenly, pulling him into his lap. Hiccup squeaked as he fell against his hard legs, trying to struggle free for a moment before giving up and crossing his arms with a huff. “You’re going to kill me one day.” He muttered. “Heels? Really?”

“They look good.” Dagur smirked in reply. "I have a surprise for you." He added in a singsong voice. Hiccup tried not to grimace. Dagur lifted him from his lap, and, without preamble, pushed him face first over the table. Part of Hiccup was annoyed, because really, did he clean for nothing around here? His headband was tugged off and Dagur’s hands brushed along his hips for a moment before hooking around the waistband of his underwear and tugging them to the ground. Hiccup huffed slightly as he grabbed the table to steady himself, carefully stepping out of them when he was prompted.

“What are you doing?” He finally asked, trying to turn around. Dagur smirked and pushed him back down.

“No peeking.” He said almost tauntingly. Hiccup grumbled under his breath. He squeaked and tensed when a cold finger pressed against his hole, closing his eyes. Dagur’s hand massaged the small of his back until he relaxed again. Hiccup whined as Dagur’s fingers curled, rubbing against all the good things inside him until he was melting against the table. It was totally unfair how well Dagur knew his body, and especially unfair that his body turned traitor and turned him into a blubbering mess. He pressed a hand to his mouth to cover his groans as Dagur’s fingers slid out, soon being replaced by something a bit bigger. He bit his lip to keep from whimpering while he was slowly speared open, until what he suddenly realized was a plug was fully seated inside him.

Opening his eyes, Hiccup squirmed slightly, a slight groan escaping him as the plug pressed against his sweet spot. Something soft and fuzzy brushed against his legs and he frowned in confusion. “Da- Master.. What..”

Dagur hushed him softly and tugged on his shoulders to help him stand up. Hiccup whined and ducked his head to hide his blush as Dagur tucked a headband that felt wider than his usual one on his head. His hand wrapped around Hiccup’s, pulling him away from the table and over to a large mirror.

Perched on his head were two curved white ears that were decidedly feline. Tilting his head, Hiccup’s eyes scanned over the tight black dress with white laces criss crossing over his chest, the cliche little apron a bit off center. The fluffy skirt puffed out awkwardly in the back, and Hiccup twisted to look behind him curiously. There, hanging from what he was pretty sure was the plug, was a sleek white  _tail._

“You look adorable.” Dagur said with a grin, guiding his face around for a kiss. Hiccup just stared at himself in the mirror for a few moments longer before tugging himself out of Dagur’s arms. He stumbled again, and with a cry of annoyance, kicked off the stupid heels before going upstairs as quickly as he could. Which, admittedly, with a plug in his ass, wasn't that fast, but he slammed the door of his bedroom behind him anyway, crawling into his bed and crossing his arms with a huff.


End file.
